I’m on my first 90 tourist days in Ukraine at the moment (expires 7 August), and during the first week of August I’ll try to do a border run for another 90-day tourist stamp. My main question is this: Will the second 90-day stamp, being technically something I shouldn’t have, prevent me from getting either WP or visa? I have an offer from a school that employs teachers legally, but they may not begin paperwork until I’m on that second stamp. I won’t have a chance to discuss it with them until Tuesday.

If the school begins the paperwork soon (during my first 90), might that eliminate the need to do a border run? It would in some countries, but I don’t know about Ukraine.

I could ask the school to go ahead and begin the process now, while I’m still within my first 90, but my understanding is that I need 9 months remaining on my current passport in order to do this (not sure about this), and I don’t have those 9 remaining months. If this 9-month rule exists, I need to get a new passport first.

Also: any recommendations as to the border crossing that currently gives the best chance of success, or any other pertinent info would be appreciated. I know some of this has been written about in past posts, but the situation seems so fluid and inconsistent here in Ukraine, past posts may be out-of-date.

In case it matters, I’m in Kiev, can’t do a border run until August, and I was planning a run to Poland over the walk-through crossing near Przemysl.

You will need to get a visa known as an "IM1". To do this you have to go to a consulate or embassy outside Ukraine. Without this, you won't be legal.
Once you have this and the work-permit that your school should arrange, a temp residence permit can be obtained. It lasts 1 year, but can be renewed without further visas.

If you leave the country and return on a 90 day visa, you will still have to leave later to get your IM1 visa.

If I were you, I would get a new passport asap (when does your passport expire?) and then arrange for the school to get on with the legalization.

Hope this helps.

If it's a decent school, they should take care of all this and advise you what to do. I suggest you discuss it with the director.
If they aren't helpful on this matter and if they don't offer to pay for the whole process, then I would advise you to look for a better employer.

Perhaps some will disagree with me, but if you trust that your employer will get you a work visa, then I suggest you just stay over your 90 days. When it is time for you to go to a Ukrainian embassy/consulate to get the official visa work done, you will have a slip of paper authorizing you to work in Ukraine. When you get to the border (most likely, the border of Poland, Moldova, or Transnistria) just show this slip of paper and your passport to the border guard, and everything should be ok. If not, you might have to pay a couple hundred gryvnias.

Perhaps some will disagree with me, but if you trust that your employer will get you a work visa, then I suggest you just stay over your 90 days. When it is time for you to go to a Ukrainian embassy/consulate to get the official visa work done, you will have a slip of paper authorizing you to work in Ukraine. When you get to the border (most likely, the border of Poland, Moldova, or Transnistria) just show this slip of paper and your passport to the border guard, and everything should be ok. If not, you might have to pay a couple hundred gryvnias.

I've heard of this being done on more than one occasion, and have never heard of it failing. There is a fine - could be 500 grvs in some cases, but not more.

However, in the OP's case, it seems that the main issue is the upcoming expiry of his/her passport.

Thanks for the replies, they’ve all been helpful. I spoke to the school director today and apparently that IM1 has been changed to a “D” visa, but the proces is identical to what Cardinal Synn described. Also good to know that the border run is not likely necessary. In fact, I may be able to leave to get the D-visa before my initial 90 expires anyway, if I can get my Trinity Cert apostilled quickly, (director didn’t seem to think my uni diploma would be necessary).

My passport expires in November, but the director didn’t seem to think that would be a problem, said the visa could probably be transferred from one passport to another. In any event, I’ll head to the US consulate very soon and look into that, maybe the temporary passport they issue will suffice.

Two remaining questions:
It’s easy enough to find firms in the UK that offer to facilitate the gov apostille, one even says that an electronic copy would be OK, but does anybody have any particular tips from personal experience? A good firm to use? Any pitfalls to avoid? Apparently the Trinity cert requires UK apostille, not Czech, where I took the course.
AND/OR
Opinions about the best nearby Ukrainian embassy/consulate to use when I go to get the D-visa?

Again, sorry if these questions have been answered before, I’m just looking for the most current info, and thanks for the help.

Yes, the director seemed absolutely certain about this. I don't know why it hadn't occurred to me to simply go to the UK embassy here and see if they can do it. I was more surprised that the uni degree didn't seem to matter. Either way, I don't think it's particularly difficult to do, judging from past posts.

There is no reason for you to jump through any hoops. The school employs you and does all the paperwork. You just do the visa bit.
It's how it works and if they don't do it that way, then what else do they "not" do?

So, I would talk to the director again and ask them to take care of the entire proccess.

I spent about a week in Crimean Black Sea resort towns a few years ago, while working in Kiev. Is this still possible, or does one need a Russian visa to visit Krim now??

Thanks,
-HDt

I'm pretty sure that you do. Many of my Russian colleagues and friends were encouraging me to go, because I could do it on a Russian visa now (though I wouldn't have needed a visa to go when it was Ukraine, but I guess they didn't realize that).

Up to now many foreign teachers in Ukraine have been able to get away with over staying (staying past the allowed 90 days) and just paying a fine at the airport when exiting Ukraine. Now the Immigration services have been cracking down on the English schools. I have personally witnessed this! If they catch you while your still in Ukraine they make you go through a humiliating deportation process which involves court! Only the higher end international schools have the means to get teachers a working visa.